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WO2009063174A1 - Procédé amélioré de production d'un alcool à partir d'une charge carbonée - Google Patents

Procédé amélioré de production d'un alcool à partir d'une charge carbonée Download PDF

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Publication number
WO2009063174A1
WO2009063174A1 PCT/GB2008/003764 GB2008003764W WO2009063174A1 WO 2009063174 A1 WO2009063174 A1 WO 2009063174A1 GB 2008003764 W GB2008003764 W GB 2008003764W WO 2009063174 A1 WO2009063174 A1 WO 2009063174A1
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WO
WIPO (PCT)
Prior art keywords
methanol
ethanol
ethanoate
reactor
synthesis gas
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2008/003764
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English (en)
Inventor
Craig Bailey
Berian John Daniel
Benjamin Patrick Gracey
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BP PLC
Original Assignee
BP PLC
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Filing date
Publication date
Application filed by BP PLC filed Critical BP PLC
Publication of WO2009063174A1 publication Critical patent/WO2009063174A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/159—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with reducing agents other than hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1516—Multisteps
    • C07C29/1518—Multisteps one step being the formation of initial mixture of carbon oxides and hydrogen for synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F14/00—Inhibiting incrustation in apparatus for heating liquids for physical or chemical purposes
    • C23F14/02—Inhibiting incrustation in apparatus for heating liquids for physical or chemical purposes by chemical means
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention relates to an improved process for the production of ethanol from methanol.
  • the present invention relates to an improved process for the production of ethanol from a carbonaceous feedstock; wherein the carbonaceous feedstock is first converted to synthesis gas which is then converted to ethanoic acid, which is then esterified and which is then hydrogenated to produce ethanol.
  • Alcohols such as ethanol
  • Synthesis gas refers to a combination of H 2 and carbon oxides produced in a synthesis gas plant from a carbon source such as natural gas, petroleum liquids, biomass and other carbonaceous materials including coal, recycled plastics, municipal wastes, or any organic material.
  • a carbon source such as natural gas, petroleum liquids, biomass and other carbonaceous materials including coal, recycled plastics, municipal wastes, or any organic material.
  • alcohol and alcohol derivatives may provide non-petroleum based routes for the production of valuable chemicals and fuels.
  • US 4122110 relates to a process for manufacturing alcohols, particularly linear saturated primary alcohols, by reacting CO with H 2 at a pressure between 2 and 25 MPa and a temperature between 150 and 400 0 C, in the presence of a catalyst, characterized in that the catalyst contains at least 4 essential elements: (a) copper (b) cobalt (c) at least one element M selected from chromium, iron, vanadium and manganese, and (d) at least one alkali metal.
  • the present invention also relates to an improved continuous process for the production of ethanol from a carbonaceous feedstock, whereby a carbonaceous feedstock is first converted into synthesis gas, which is subsequently converted into ethanol, characterised by the following consecutive steps: 1) introducing a carbonaceous feedstock, into a synthesis gas generation unit to produce synthesis gas,
  • the 'dew point temperature' is a threshold temperature, for example, for a given pure component or mixture of components, at a given pressure, if the system temperature is raised to above the dew point temperature, the mixture will exist as a dry gas. Likewise below the dew point temperature, the mixture will exist as a vapour containing some liquid.
  • - 'Gas' and/or 'gas phase' are defined as a pure component, or mixture of components, that are above the dew point temperature.
  • - 'Gas hourly space velocity' (GHSV) is defined as the volume of gas fed per unit volume of catalyst per hour, at standard temperature (0 0 C) and pressure (0.101325 MPa).
  • - 'Liquid hourly space velocity' (LHSV) is defined as the volume of liquid fed per unit volume of catalyst per hour.
  • the synthesis gas feedstock, a mixture of carbon oxide(s) and H 2 , that is used to produce the methanol feed stream is preferably produced from a carbonaceous feedstock.
  • Natural gas commonly contains a range of hydrocarbons (e.g. C 1 -C 3 alkanes), in which methane predominates.
  • natural gas will usually contain nitrogen, CO 2 and sulphur compounds.
  • the nitrogen content of the feedstock is less than 40 mol %, more preferably less than 10 mol % and most preferably less than 2 mol %.
  • the synthesis gas may be obtained by catalytic partial oxidation of hydrocarbonaceous material in a microstructured reactor as exemplified in IMRET 3: Proceedings of the Third International Conference on Microreaction Technology, ed. W. Ehrfeld, Springer Verlag, 1999, pages 187-196.
  • the synthesis gas may be obtained by short contact time catalytic partial oxidation of hydrocarbonaceous feedstocks as described in EP 0303438.
  • the molar ratio, (H 2 - CO 2 ) .”(00+CO 2 ), of the synthesis gas stream exiting the synthesis gas generation unit(s) is greater than 1.6, more preferably greater than 1.8 and most preferably greater than 2.0.
  • the molar ratio, (H 2 -CO 2 ):(CO+CO 2 ), of said synthesis gas stream exiting the synthesis gas generation unit(s) is less than 3.0, preferably less than 2.75, more preferably less than 2.4 and most preferably less than 2.2.
  • the stream exiting the methanol synthesis reactor is subsequently purified to remove said by-products by any methods known to those skilled in the art.
  • the iridium carbonylation catalyst concentration in the liquid reaction composition is in the range 100 to 6000 ppm by weight of iridium, more preferably 700 to 3000 ppm by weight of iridium.
  • Ethanoic acid may advantageously be used as a solvent for said carbonylation reaction.
  • any sulphonic acid which has a de-sulphonation temperature greater or equal to that of p-toluene sulphonic acid is preferred as a catalyst.
  • the de-sulphonation temperature of a sulphonic acid is defined as "the minimum temperature at which the reaction (de-sulphonation) occurs at a practical rate at atmospheric pressure" (see page 429 of E. E. Gilbert, Sulphonation and Related Reactions, Interscience, 1965).
  • the de- sulphonation temperature of p-toluene sulphonic acid is 186 0 C hence the sulphonic acids used in the present invention preferably have de-sulphonation temperatures in excess of this and preferably in excess of 190 0 C.
  • the temperature of esterification is preferably greater than 80 0 C and more preferably is in the range of 125 tol85 0 C.
  • the process may be operated continuously or batchwise.
  • a suitable method for carrying out the esterification continuously is described in EP0009886.
  • the reaction mixture may also contain in addition to the catalyst between 0.1 and 1 wt % of a corrosion inhibitor to reduce corrosion of the vessel.
  • a corrosion inhibitor is copper as a salt for example copper ethanoate.
  • the stream exiting the esterification reactor comprises methyl and/or ethyl ethanoate, as well as unreacted ethanoic acid, ethanol and/or methanol, esterification catalyst and water.
  • This stream may be continuously removed from the reactor by distillation whilst the reaction occurs.
  • the stream exiting the esterification reactor is purified to remove said ethanoic acid and esterification catalyst, before its introduction into the hydrogenation unit.
  • the ethanoate stream contains preferably less than 5 ppm wt of esterification catalyst, more preferably less than 1 ppm wt, most preferably less than 0.1 ppm wt.
  • the ethanoate stream contains preferably less than 5 wt % of ethanoic acid, more preferably less than 1 wt %, even more preferably less than 0.1wt % and most preferably less than 100 ppm wt.
  • a methyl ethanoate/methanol mixture and/or an ethyl ethanoate/ethanol mixture can also advantageously be used together with the ethanoate as a feed to the hydrogenation unit; this is particularly advantageous because it considerably simplifies the purification process.
  • water can also be introduced into the hydrogenation unit.
  • said water represents between 0.5 and 20 mol %, preferably between 0.5 and 15 mol % and most preferably between 1 and 5 mol % of the total liquid feed (ethanoate, alcohol and water) to the hydrogenation reactor.
  • the applicants have unexpectedly found an additional advantage whereby a methyl ethanoate/methanol mixture and/or an ethyl ethanoate/ethanol mixture from the esterification reactor is used as the feed for the hydrogenation unit.
  • Said advantage being that the applicants were able to retain a high selectivity towards the production of ethanol, whilst using the aforementioned feed, as well as providing a method for reducing the exotherm of the hydrogenation reaction, thus increasing the lifetime of the hydrogenation catalyst.
  • This is particularly advantageous when using an adiabatic mode of operation for the hydrogenation reaction.
  • Preferably at least a part, most preferably all, of the H 2 fed into the hydrogenation unit emanates from the synthesis gas generation procedure (i.e.
  • the H 2 content can be further increased by subjecting the said synthesis gas to a water gas shift reaction and a subsequent H 2 separation.
  • the applicants have unexpectedly found that when operating the present invention, by using the aforementioned cryogenic separation to separate the synthesis gas, or a method that results in a similar standard of separation, it is advantageous to obtain and use substantially pure H 2 to feed the hydrogenation reactor.
  • the H 2 stream may originate from a variety of other chemical processes, including ethene crackers, styrene manufacture and catalytic reforming.
  • the main commercial processes for purposeful generation of H 2 are autothermal reforming, steam reforming and partial oxidation of hydrocarbonaceous feedstocks such as natural gas, coal, coke, deasphalter bottoms, refinery residues and biomass.
  • H 2 may also be produced by electrolysis of water.
  • the catalyst(s) employed in the hydrogenation unit is selected from any of the following:
  • the catalyst(s) employed in the hydrogenation unit is a copper-based catalyst, more preferably comprising copper and zinc, most preferably consisting of copper-zinc-oxide.
  • the catalyst(s) employed is heterogeneous.
  • the hydrogenation process may be operated in a gas phase, or a mixed gas/liquid phase regime.
  • the mixed gas/liquid phase regime is where the reactant mixture, at the reactor conditions, is below the dew point temperature.
  • the hydrogenation reaction can be conducted in adiabatic or isothermal mode; where adiabatic mode of operation is preferred.
  • Suitable reactors include single, or a plurality, of adiabatic bed reactors which can be used in series or parallel.
  • heat exchangers and/or intercoolers and/or additional reactant and/or recycle of intermediates can be employed in between successive reactors to control the reaction temperature.
  • the preferred adiabatic temperature rise is less than 50 °C, preferably less than 25 °C and most preferably less than 10 °C.
  • the preferred use of adiabatic reactors is in series.
  • the adiabatic reactors may be operated at different temperatures depending on composition of the individual reactor feeds.
  • the hydrogenation can also be conducted in multi-tubular reactors in which case a cooling/heating medium is circulated around the tubes to control the temperature.
  • a cooling/heating medium is circulated around the tubes to control the temperature.
  • the preferred gradient is less than 50 0 C preferably less than 25 0 C most preferably less than 10 0 C.
  • the preferred flow regime in this type of reactor is turbulent rather than laminar, this corresponds to a Reynolds number greater than 2100 (where the velocity is approximated by velocity in an unpacked tube).
  • the hydrogenation reaction can also be conducted in other reactor types such as fluidised bed, spinning basket and buss loop, heat exchanger reactors.
  • a mixed liquid/gas phase hydrogenation reaction can be conducted with co-flow or counterflow of the H 2 and gas to the liquid (e.g. a bubble reactor).
  • the preferred mode of operation of gas/liquid reactors is co-flow, also known as trickle bed operation; this can be conducted in at least one tubular and/or multi-tubular reactor in series.
  • the hydrogenation reaction may change from a mixed gas/liquid phase to a fully gas phase reaction, as the reaction proceeds down the reactor.
  • the mixed phase hydrogenation can also be conducted in other types of reactors, or within a combination of different reactors, for example in a slurry or stirred tank reactor with, or without, external circulation and optionally operated as a cascade or stirred tanks, a loop reactor or a Sulzer mixer-reactor.
  • the ester liquid substrate introduced into the hydrogenation unit preferably has an LHSV preferably less than 1Oh "1 , more preferably less than 5b. "1 and most preferably less than 3b. "1 ; for example, a typical LHSV for normal operation is approximately Ih '1 .
  • FIG 2 is a simplified flow diagram for one embodiment of the present invention and an improved process for the production of ethanol from a carbonaceous feedstock is shown.
  • a carbonaceous feed stream is supplied to the synthesis gas generation unit, 201, through line 221 and a stream comprising water and/or oxygen is supplied to the synthesis gas generation unit through line 222.
  • Synthesis gas from the synthesis gas generation unit is passed to a synthesis gas separation zone, 202, through line 223.
  • crude synthesis gas from the synthesis gas generation zone is separated to provide synthesis gas as well as CO and H 2 streams.
  • Water is removed from the synthesis gas separation unit through line 240.
  • Synthesis gas from the synthesis gas separation zone is fed to the methanol synthesis zone, 203, through line 224.
  • synthesis gas is converted to methanol in a methanol synthesis reactor and methanol is separated from the methanol synthesis reactor product stream.
  • a purge stream is taken from the methanol synthesis zone through line 242 to control the build up of diluent gases in the methanol synthesis zone.
  • Methanol is fed from the methanol synthesis zone to the carbonylation reactor, 204, through line 227.
  • CO from the synthesis gas separation zone is fed to the carbonylation reactor through line 225.
  • Methanol and CO are reacted together in the carbonylation reactor in a liquid reaction composition which comprises ethanoic acid, an iridium catalyst, methyl iodide, water and at least one promoter.
  • a purge stream is taken from the carbonylation reactor through line 241 to control the build up of diluent gases in the carbonylation reactor.
  • the liquid reaction composition from the carbonylation reactor is passed to an ethanoic acid separation and purification zone, 205, through line 228.
  • Ethanoic acid is separated from the carbonylation reaction liquid reaction composition in the ethanoic acid separation and purification zone.
  • a stream comprising the iridium catalyst, methyl iodide, water and promoter is returned to the carbonylation reactor from the ethanoic acid separation and purification zone through line 239.
  • Ethanoic acid is further purified of halide compounds in the ethanoic acid separation and purification zone.
  • Methanol and CO are reacted together in the carbonylation reactor in a liquid reaction composition which comprises ethanoic acid, an iridium catalyst, methyl iodide, water and at least one promoter.
  • a purge stream is taken from the carbonylation reactor through line 341 to control the build up of diluent gases in the carbonylation reactor.
  • the liquid reaction composition from the carbonylation reactor is passed to an ethanoic acid separation and purification zone, 305, through line 328. Ethanoic acid is separated from the carbonylation reaction liquid reaction composition in the ethanoic acid separation and purification zone.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne un procédé continu et amélioré de production d'éthanol à partir d'une charge carbonée; la charge carbonée étant d'abord convertie en un gaz de synthèse qui est alors converti en acide éthanoïque, qui est ensuite estérifié puis qui est hydrogéné pour produire de l'éthanol.
PCT/GB2008/003764 2007-11-14 2008-11-07 Procédé amélioré de production d'un alcool à partir d'une charge carbonée Ceased WO2009063174A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07254448 2007-11-14
EP07254448.9 2007-11-14

Publications (1)

Publication Number Publication Date
WO2009063174A1 true WO2009063174A1 (fr) 2009-05-22

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PCT/GB2008/003764 Ceased WO2009063174A1 (fr) 2007-11-14 2008-11-07 Procédé amélioré de production d'un alcool à partir d'une charge carbonée
PCT/GB2008/003759 Ceased WO2009063173A1 (fr) 2007-11-14 2008-11-07 Procédé de production d'alcool amélioré à partir d'une charge carbonée

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PCT/GB2008/003759 Ceased WO2009063173A1 (fr) 2007-11-14 2008-11-07 Procédé de production d'alcool amélioré à partir d'une charge carbonée

Country Status (10)

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US (2) US8378153B2 (fr)
EP (3) EP2060555A1 (fr)
CN (2) CN103787831B (fr)
CA (1) CA2705720C (fr)
EA (1) EA016551B1 (fr)
ES (1) ES2475971T3 (fr)
MY (1) MY155707A (fr)
PL (1) PL2231568T3 (fr)
SG (1) SG186001A1 (fr)
WO (2) WO2009063174A1 (fr)

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US7884253B2 (en) 2008-12-11 2011-02-08 Range Fuels, Inc. Methods and apparatus for selectively producing ethanol from synthesis gas
EP2287145A1 (fr) 2009-08-12 2011-02-23 BP p.l.c. Procédé pour la purification d'éthylène
WO2012149137A1 (fr) 2011-04-26 2012-11-01 Celanese International Corporation Procédé de production d'éthanol à partir d'une charge d'acide acétique et d'une charge d'acétate d'éthyle recyclé
WO2012148510A1 (fr) 2011-04-26 2012-11-01 Celanese International Corporation Procédé de production d'éthanol faisant appel à de multiples lits ayant chacun des catalyseurs différents
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US8378153B2 (en) 2013-02-19
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US8907140B2 (en) 2014-12-09
MY155707A (en) 2015-11-13
CN103787831A (zh) 2014-05-14
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US20110004034A1 (en) 2011-01-06
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